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16. Vinny Cha$e

Vinny Cha$e knows how to do the high-low thing well. The Harlem native rocks high-end outerwear with vintage sports apparel, and parody T-shirts with Yeezy IIs with Louis Vuitton backpack on the side. Cha$e has proved he can put together complete looks, but his greatest contribution to the style world might be something he designed—this. The rapper is the man behind the "Luxy Mask" that we've seen both 2 Chainz and Justin Bieber recently don.